Great Barrington holiday lettings

We found 665 holiday rentals — enter your dates for availability

Select from 98 homes, 15 cottages and other holiday rentals in Great Barrington to find one that's perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the amenities that you need and want, including Wi-Fi and parking. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Great Barrington

Showing deals for:26 Dec - 2 Jan

Image gallery for General Williams Estate House Lenox/Stockbridge

Front of house
9.8 out of 10, Exceptional, (110 reviews)
Exceptional
(110 reviews)

General Williams Estate House Lenox/Stockbridge

Stockbridge, MA

8% off
Price is £6,796
for 7 nights, 1 home
£971 per night
includes taxes & fees
General Williams Estate House Lenox/Stockbridge

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Find out more about Great Barrington

Find out more about Great Barrington

Why visit Great Barrington

  • Adventure sports: Great Barrington is renowned for skiing and a variety of outdoor activities, perfect for thrill-seekers.
  • Historic exploration: Discover charming historic houses and local shrines that reflect the area's rich heritage.
  • Stunning scenery: Enjoy breathtaking views and tranquil spots for relaxation amidst beautiful landscapes.
  • Charming local vibe: Experience lively local eateries and shops, offering a warm community atmosphere.
  • Varied accommodation: Choose from a range of holiday rentals, including cosy cottages and modern condos, to suit any preference.

Popular types of accommodation in Great Barrington

If you're considering a getaway to Great Barrington, you're in for a treat! This charming destination offers a variety of holiday rentals to suit your needs. The most popular options include houses, cosy cottages, and modern condos. Whether you're seeking spacious bedroom rentals or properties with extra amenities, you'll find the perfect holiday rental in Great Barrington to create lasting memories.

  • Houses: The top choice for visitors to Great Barrington, offering spacious and comfortable settings ideal for families or groups.
  • Condos: A popular alternative, these self-contained units provide a blend of convenience and modern amenities.
  • Cottages: Quaint and charming, cottages offer a delightful retreat amidst scenic surroundings.
  • Apartments: Perfect for a more urban feel, apartments provide a home-away-from-home experience.
  • Cabins: Embrace the outdoors with rustic cabins that are perfect for nature enthusiasts.**

Top attractions in and around Great Barrington

Great Barrington is an ideal destination for skiing and adventure sports, offering a variety of attractions for visitors. You can explore historic houses, national and state parks, and local shrines, catering to those seeking outdoor activities, cultural experiences, and thrilling adventures. Whether you're keen on skiing or immersing yourself in the area's rich history, Great Barrington has something for everyone to enjoy.

  • National Shrine of the Divine Mercy: A serene and spiritually enriching site, this shrine offers a peaceful atmosphere and beautiful architecture, perfect for contemplation and prayer, set in a picturesque landscape just 4.3km from Great Barrington.
  • Lake Buel: This idyllic lake features a charming beach and stunning scenery, ideal for outdoor activities and romantic picnics, right within Great Barrington.
  • Housatonic River: A scenic river that provides a backdrop for outdoor adventures such as kayaking and fishing, located a mere 62m from the town, enhancing your natural exploration.

Things to do recommended for couples

For a romantic getaway in Great Barrington, indulge in a day at Ski Butternut for some exhilarating skiing, followed by enchanting melodies at Tanglewood Music Center just 6.8km away. Cap off your adventure with a delightful tasting at Les Trois Emme Winery, perfect for couples seeking romance.

Things to do recommended for families

Your family will love exploring Lake Mansfield Park in Great Barrington, a lovely spot for relaxation and wellness. For a bit of adventure, head to Tyringham Cobble, just 5.0km away, or discover the serene Goose Pond Reservation, located 6.8km from town.

Things to do recommended for groups

Groups visiting Great Barrington can enjoy a scenic hike along the Housatonic River Walk, experience culture and entertainment at the Mahaiwe Performing Arts Center, and indulge in shopping at the Lee Premium Outlets, located a short drive away, offering a delightful mix of retail and leisure.

What do I need to keep in mind when booking a vacation in 'Great Barrington

When planning your trip, whether you're journeying with a group, enjoying a family getaway, bringing along your pets, or seeking extended stays, it's essential to refine your search according to your key priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Great Barrington with a group: Think about how many bedrooms you'll require, along with additional features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Great Barrington with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Great Barrington: For many, a family holiday isn’t truly fulfilling without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. The majority of these pet-friendly accommodations offer feeding bowls and beds, ensuring that all members of the family feel at home.
  • Planning for a long term stay visiting Great Barrington: If you're seeking holiday rentals with offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include features like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Great Barrington

Great Barrington, Massachusetts, offers a delightful blend of adventure and relaxation, perfect for a memorable holiday. With its stunning scenery and vibrant atmosphere, you can enjoy outdoor seating in lively local spots. Explore charming nearby towns and indulge in family-friendly activities, or find a romantic nook to unwind. It's an ideal location for skiing and sports, making it a fantastic getaway for those seeking both thrill and tranquillity.

  • Lenox: Situated 7.5km from Great Barrington, Lenox is renowned for its vibrant entertainment scene, making it an ideal destination for a romantic getaway or family adventure. Visitors can enjoy a variety of activities, including music concerts and theatre performances, as well as skiing during the winter months. The picturesque landscape features beautiful lakes and mountains, providing the perfect backdrop for outdoor pursuits. Additionally, the town hosts an array of event venues, making it a popular spot for conferences and gatherings.
  • The Berkshires: Located 6.8km away from Great Barrington, The Berkshires is a haven for outdoor enthusiasts seeking adventure and stunning scenery. The area is famous for its excellent skiing opportunities, with numerous ski fields and resorts to explore. Visitors can revel in the natural beauty of the lakes and mountains while engaging in various outdoor activities. The Berkshires also boasts charming communities and local events, ensuring a memorable experience for all who venture into this enchanting region.
  • Stockbridge: Just 4.3km from Great Barrington, Stockbridge is a charming town steeped in culture and history. It offers a delightful blend of romantic experiences and entertainment, with a thriving arts scene featuring music concerts and theatre performances. Outdoor activities are abundant, particularly around its scenic lakes and notable landmarks, including monuments and shrines. Stockbridge is the perfect place to immerse yourself in local culture while enjoying the stunning natural surroundings.

Best time to go to Great Barrington

If you're planning a trip to Great Barrington, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverageAverage
February24.8°F (-4.0°C)Light RainMostly CloudyAverageAverage
March32.5°F (0.3°C)Light RainMostly CloudyAverageSlightly Low
April44.2°F (6.8°C)Light RainMostly CloudyAverageSlightly Low
May55.9°F (13.3°C)Light RainMostly SunnyAverageAverage
June63.7°F (17.6°C)Light RainMostly SunnySlightly HighAverage
July69.8°F (21.0°C)Light RainMostly SunnySlightly HighSlightly High
August67.8°F (19.9°C)Light RainMostly SunnySlightly HighSlightly High
September60.8°F (16.0°C)Light RainMostly SunnyAverageAverage
October49.8°F (9.9°C)Light RainMostly SunnySlightly LowSlightly Low
November37.8°F (3.2°C)Light RainMostly SunnySlightly LowAverage
December29.7°F (-1.3°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your next holiday? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient space to plan new holidays, pick up from where you last left off, or review and organise your travel arrangements. Any properties you've previously saved or booked can now be easily located under Potential, Upcoming, or Current Trips. To start using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

The lively city of Great Barrington awaits you

The area's live music and theatre scene are just some of the reasons to come on holiday to Great Barrington. Well known for its rock climbing, hiking and cafes, this scenic city won't disappoint. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Great Barrington

Are you looking for attractions to see during your stay? You'll be sure to enjoy Great Barrington for its hiking and skiing. Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Great Barrington a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Ski Butternut (2.3 mi / 3.7 km)
  • Catamount Ski Area (6.3 mi / 10.1 km)
  • Wyndhurst Golf & Club (11.3 mi / 18.1 km)
  • Wood's Pond (12 mi / 19.3 km)
  • Kennedy Park (13.4 mi / 21.6 km)
  • Furnace Brook Winery at Hilltop Orchards (13.8 mi / 22.2 km)

Exploring the natural landscape of Great Barrington

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Great Barrington is a great place to get out in nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Housatonic River Walk (0.1 mi / 0.2 km)
  • Housatonic River (0.1 mi / 0.2 km)
  • Lake Mansfield Park (0.7 mi / 1.1 km)
  • Lake Buel (4.8 mi / 7.7 km)
  • Naumkeag Museum (6.9 mi / 11.1 km)
  • Berkshire Botanical Garden (7.4 mi / 11.8 km)

Seasonal weather averages in Great Barrington

Travellers enjoy Great Barrington for its skiing. To make the most of the cold weather activities, you might consider visiting in January, March, February or November, when snowfall averages 18 cm and temperatures average -2°C.

Transport options to and around Great Barrington

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 16.2 mi (26.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Hudson, NY (HCC-Columbia County), which is 19.2 mi (30.9 km) away.

Frequently asked questions

What is the best area to stay in Great Barrington when booking a holiday rental?
When considering a holiday rental in Great Barrington, Massachusetts, the downtown area is an excellent choice. This vibrant neighbourhood offers a charming mix of boutique shops, delightful eateries, and art galleries, all within walking distance. Staying here provides easy access to the renowned Mahaiwe Performing Arts Centre, which hosts a variety of shows and events, making it a cultural hub. Additionally, the picturesque Lake Mansfield is nearby, superb for leisurely strolls or a peaceful day by the water.

Another appealing area to consider is the Housatonic neighbourhood, located just north of the main town. Housatonic boasts a more relaxed atmosphere, with scenic views and a close-knit community feel. The nearby Housatonic River offers opportunities for kayaking and fishing, while the charming local cafes provide a welcoming spot to unwind. This area has a modest selection of holiday rentals, ensuring a more tranquil experience away from the hustle and bustle of downtown.
How much does it cost to rent a holiday home in Great Barrington?
Prices for holiday rentals in Great Barrington vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Great Barrington to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Great Barrington holiday house rentals?
You can find great discounts on house rentals in Great Barrington on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Great Barrington ski resort rentals?
For ski resort rentals in Great Barrington, Massachusetts, travellers should consider properties near the popular Butternut Ski Area, which is just a short drive from the town centre. The area offers a variety of accommodations, ranging from cosy chalets to spacious cabins, many of which feature amenities like wood-burning stoves, hot tubs, and fully equipped kitchens. These properties are ideal for families or groups looking to enjoy a ski getaway with all the comforts of home.

In the town of Great Barrington itself, visitors can find charming inns and boutique hotels that provide easy access to both the ski slopes and local attractions. Many of these lodgings come with complimentary breakfast, on-site dining options, and access to recreational facilities like saunas or fitness rooms. The vibrant downtown area is also worth exploring, with its selection of shops, cafes, and restaurants offering a taste of local culture.
What is the most popular type of holiday rental accomodation in Great Barrington?
In Great Barrington, holiday houses are the most popular type of rental accommodation, with approximately 81 available throughout the area. These properties are typically situated in scenic neighbourhoods, providing guests with easy access to local attractions such as the Mahaiwe Performing Arts Centre and the nearby Berkshire Mountains. Most holiday houses come equipped with spacious living areas, fully stocked kitchens, and outdoor decks or patios, ideal for enjoying the beautiful surroundings.
Are there any family house rentals in Great Barrington?
In Great Barrington, Massachusetts, there are numerous family-friendly house rentals available, with around 82 options to choose from. This charming town is located in the scenic Berkshires, offering a great backdrop for family getaways. Properties in the area often come with spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for children to play or for family gatherings.
Can I rent a holiday home with a pool or hot tub in Great Barrington?
In Great Barrington, there are several holiday homes available for rent that feature pools and hot tubs, with approximately 19 options to choose from. This picturesque town, located in the Berkshires, is known for its charming downtown area and beautiful natural surroundings. Travellers can find rentals in neighbourhoods like the scenic Lake Buel and along the Housatonic River, where properties often boast stunning views of the mountains and easy access to outdoor activities.
Can I find long-stay holiday rentals in Great Barrington?
A long-stay holiday rental in Great Barrington is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Great Barrington?
In Great Barrington, there are numerous pet-friendly house rentals available, offering a delightful retreat for travellers with pets. Many of these accommodations come equipped with modern amenities such as spacious living areas, fully stocked kitchens, and outdoor spaces where pets can roam freely.

The town is surrounded by beautiful landscapes, providing ample opportunities for outdoor activities. Nearby, the picturesque Monument Mountain offers hiking trails that are great for exploring with your furry companion. Additionally, the quaint downtown area features pet-friendly cafes and shops, allowing you to enjoy the local culture without leaving your pet behind.
Are there any remote work holiday rentals in Great Barrington?
In Great Barrington, Massachusetts, there is a wide selection of remote work holiday rentals available, with approximately 102 properties catering specifically to those needing a workspace. This charming town in the Berkshires offers a superb blend of scenic beauty and modern amenities, making it an ideal location for remote workers.

Travellers can expect rentals equipped with essential amenities such as high-speed Wi-Fi, dedicated desk spaces, ergonomic chairs, and even office areas, ensuring a productive work environment. Many properties also include features like comfortable living areas, fully equipped kitchens, and outdoor spaces for relaxation during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Great Barrington holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Great Barrington with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Great Barrington?
In Great Barrington, popular holiday rental amenities include fully equipped kitchens, which are essential for those looking to prepare their own meals during their stay. Most rentals feature cookware, dishware, and utensils, along with essential appliances such as stovetops, refrigerators, and microwaves. This allows guests to enjoy the flexibility of cooking at home while being close to local attractions such as the picturesque downtown area, the scenic Berkshire hills, and the nearby hiking trails.
When is the best time to visit Great Barrington for a holiday rental?
The best time to visit Great Barrington for a holiday rental is during the summer months, particularly July, when the area comes alive with vibrant outdoor activities and events. This peak season, stretching from June to August, sees an influx of visitors keen to enjoy the warm weather and picturesque landscapes that the Berkshires have to offer.

In July, temperatures typically hover in the mid to high 20s Celsius, making it an ideal time for hiking, biking, and exploring the charming downtown area filled with boutiques and eateries. The lush surroundings provide a beautiful backdrop for outdoor concerts and festivals, creating a lively and welcoming atmosphere for travellers.

For those looking to travel on a budget, November offers a quieter experience with the added charm of early winter scenery. While it's outside the peak season, this time allows for peaceful exploration of Great Barrington's natural beauty and an opportunity to enjoy the area's local art and culture without the crowds.
How early should I book a Great Barrington holiday rental?
Book your Great Barrington holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Great Barrington?
In Great Barrington, visitors can enjoy a variety of attractions that highlight the area's natural beauty and cultural offerings. The downtown area features a charming selection of shops, cafés, and restaurants, great for leisurely strolls and dining. The Mahaiwe Performing Arts Centre hosts a range of events, including concerts and theatre performances, appealing to those interested in the arts.

Just a short drive from the town centre, the picturesque Monument Mountain offers hiking trails with stunning views, making it a popular spot for outdoor enthusiasts. Additionally, the nearby Berkshire Botanical Garden provides a serene setting for nature lovers, showcasing a variety of plants and seasonal blooms.
Can I change or cancel my Great Barrington home rental booking on Vrbo?
To find Great Barrington holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Great Barrington holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Holiday Rental options in Great Barrington
Mountain holiday rentals in Great Barrington
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Holiday rentals with pool in Great Barrington
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Pet-friendly holiday rentals in Great Barrington
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Holiday rentals with hot tub in Great Barrington
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Ski holiday rentals in Great Barrington
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